In this installment of winter riding and how to enjoy it, or at least survive, I’m focusing on the all-important toes and feet. Keeping this area of the body warm and dry when the temperature drops below freezing can be a struggle. With the proper footwear though, a trail ride or commute to work can be as easy as slipping on a pair of socks.

As with any cold weather riding gear, the layers used should first block the wind, then provide warmth, while managing perspiration. The climate you live in will dictate the footwear and layers used, but here in the north a full range of options is beneficial for the fall and winter months and the huge weather changes experienced from day to day, or even from morning to night. Where you ride is also a factor, but I use the same footwear for both commuting and mountain biking.

My biggest dilemma used to be keeping my feet warm and dry without causing discomfort to my toes when wearing thick socks by squishing them into the toe-box of a shoe. As the weather becomes chilly, below 50 degrees, my typical transition begins by wearing a thicker wool sock and adding neoprene toe covers to the outside of my mountain bike shoes. Just covering the shoe vents and blocking some of the wind from directly contacting my feet is enough to keep me happy. The problem with toe or shoe covers is that they end up ripping when used for mountain biking.

Unfortunately the temperature doesn’t stop falling at 50 degrees and my ankles are the first to feel the cold of the morning commute. Around the 40 degree mark, or if it’s raining, I upgrade my footwear to a full-fledged pair of riding boots like the ones pictured at the top. There are many options on the market depending on your budget and needs, but Lake, Northwave, Sidi and many others offer clipless compatible boots that are warm, cover the ankles, and offer some degree of water resistance or a waterproof lining like Gore-Tex. They also have no vents and therefore block the wind adequately.

When shopping for riding boots, take the thickest sock that you would ride in with you and try the boot on with that sock. I recommend purchasing a pair of boots that is up to one size larger than your normal size. Having a larger size boot will allow you to make changes to the insoles and give your toes room to move as different thickness of socks are used. I like to wear over-the-calf, wool hunting socks for their breathability and warmth. If it’s really cold I may also add a liner sock underneath the wool sock. The key to warmth is to allow blood to circulate to the toes, while creating a pocket of warm air inside your footwear. If your toes are smashed in the shoe they will become cold or go numb, neither of which is comfortable.

Most of the insoles that come with the boots are on the thin side and replacing them with thicker insoles will make the boot fit more snug. Pull the supplied insole out of the boot and inspect its thickness and quality, or take your favorite insole with you and try the boot on with it in place. The bottom of your foot is going to be exposed to the cold too, as well as snow and water during hike-a-bike sections. Ask yourself if you would use the provided insole in a hiking boot? If not, head to an Army Surplus store. They carry thick wool insoles with a moisture barrier for around five dollars that offer protection for the bottom of you feet. I use an Aline insole with wedges to keep my knees in line with the pedal spindle. The size larger shoe allows me to use this insole in conjunction with the stock insole, which I cut to custom fit the toe area. Using two insoles also allows me to remove one if I have to wear Eskimo grade socks or if I use a heated footbed or toe warmers during an all-day ride.

On a side note, I have narrow feet and have ridden in two different brands of boots and many shoes. In most shoes and both boots, I’ve felt like the heel cup has been too roomy, which allows my heel to slide around and causes a blister. Tying the boot tight enough to correct this has created sore spots on the top of my foot, even with thick socks. A simple fix for heel slop is to cut a strip of sticky-backed bar tape from a roll and adhere it to the inside of the heel cup. It’s tacky enough to remain in place, but easy enough to remove or reposition if needed.

Once you have boots that you feel comfortable wearing, the outside of the boot should be weather treated. To add longevity and water repellency to the exterior I apply mink oil or Nikwax. Mink oil is pretty inexpensive, just a few bucks, and Nixwax is around eight dollars a tube but both work awesome. Whether you treat the boot with a spray or a rub-in-compound, be sure that if your boots have a waterproof lining, like Gore-Tex, that the product used on the outside is compatible with it. Those are the tricks I use for warm feet. If you have some of your own, share them in the comments below.